NP-MRD: Showing NP-Card for Baicalein (NP0047774)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:44 UTC

Updated at

2024-09-03 04:18:54 UTC

NP-MRD ID

NP0047774

Natural Product DOI

https://doi.org/10.57994/1560

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Baicalein

Description

5,6,7-Trihydroxy-2-phenyl-4H-chromen-4-one, also known as 5,6,7-trihydroxyflavone or baicalein (old), belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 5,6,7-Trihydroxy-2-phenyl-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one is found, on average, in the highest concentration within welsh onions. This could make 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one a potential biomarker for the consumption of these foods. Baicalein is found in Agrobacterium rhizogenes, Austrocylindropuntia subulata, Cephalocereus senilis, Eucommia ulmoides, Oroxylum indicum , Plantago major , Pueraria montana, Scutellaria alpina, Scutellaria altissima, Scutellaria baicalensis , Scutellaria galericulata, Scutellaria lateriflora , Scutellaria oreophila, Scutellaria orientalis, Scutellaria spp., Scutellaria squarrosa, Scutellaria strigillosa, Stachys annua, Stellera chamaejasme and Trifolium pratense . Baicalein was first documented in 2000 (PMID: 10724177). A trihydroxyflavone with the hydroxy groups at positions C-5, -6 and -7 (PMID: 15853750) (PMID: 22891631) (PMID: 23098745).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309181710002D          

 20 22  0  0  0  0            999 V2000
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H

> <INCHI_KEY>
FXNFHKRTJBSTCS-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.67212923977192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
2.706689133666666

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.345448503335756

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.75503315937457

> <JCHEM_PKA_STRONGEST_BASIC>
-5.367543135658884

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
72.91390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
baicalein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-17         0                                  
HETATM    1  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    9   11                                                       
CONECT    7   10   12                                                       
CONECT    8    4    5   11                                                  
CONECT    9    6   13   16                                                  
CONECT   10    7   14   17                                                  
CONECT   11    6    8   20                                                  
CONECT   12    7   13   20                                                  
CONECT   13    9   12   15                                                  
CONECT   14   10   15   18                                                  
CONECT   15   13   14   19                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
5,6,7-Trihydroxyflavone	ChEBI
Baicalein (old)	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2369 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one

Traditional Name

baicalein

CAS Registry Number

491-67-8

SMILES

OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H

InChI Key

FXNFHKRTJBSTCS-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agrobacterium rhizogenes	LOTUS Database	35616633
Allium fistulosum	FooDB	PHENOL EXPLORER
Austrocylindropuntia subulata	Plant	KNApSAcK
Cephalocereus senilis	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Oroxylum indicum	Plant	KNApSAcK
Plantago major	Plant	KNApSAcK
Pueraria montana	LOTUS Database	35616633
Scutellaria alpina	LOTUS Database	35616633
Scutellaria altissima	LOTUS Database	35616633
Scutellaria baicalensis	Plant	KNApSAcK
Scutellaria galericulata	LOTUS Database	35616633
Scutellaria lateriflora	Plant	KNApSAcK
Scutellaria oreophila	Plant	KNApSAcK
Scutellaria orientalis	LOTUS Database	35616633
Scutellaria spp.	Plant	KNApSAcK
Scutellaria squarrosa	LOTUS Database	35616633
Scutellaria strigillosa	LOTUS Database	35616633
Stachys annua	LOTUS Database	35616633
Stellera chamaejasme	LOTUS Database	35616633
Trifolium pratense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

5-hydroxyflavonoid
6-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:2979 )
flavones (C10023 )
Flavones and Flavonols (C10023 )
Flavones and Flavonols (LMPK12111095 )
a flavone (CPD-12724 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.19	ALOGPS
logP	2.71	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.76	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.91 m³·mol⁻¹	ChemAxon
Polarizability	26.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0134890

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Baicalein

METLIN ID

Not Available

PubChem Compound

5281605

PDB ID

Not Available

ChEBI ID

2979

Good Scents ID

Not Available

References

General References

Nagashima S, Hirotani M, Yoshikawa T: Purification and characterization of UDP-glucuronate: baicalein 7-O-glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures. Phytochemistry. 2000 Mar;53(5):533-8. doi: 10.1016/s0031-9422(99)00593-2. [PubMed:10724177 ]
Huang Y, Tsang SY, Yao X, Chen ZY: Biological properties of baicalein in cardiovascular system. Curr Drug Targets Cardiovasc Haematol Disord. 2005 Apr;5(2):177-84. doi: 10.2174/1568006043586206. [PubMed:15853750 ]
Oh SB, Park HR, Jang YJ, Choi SY, Son TG, Lee J: Baicalein attenuates impaired hippocampal neurogenesis and the neurocognitive deficits induced by gamma-ray radiation. Br J Pharmacol. 2013 Jan;168(2):421-31. doi: 10.1111/j.1476-5381.2012.02142.x. [PubMed:22891631 ]
Sithisarn P, Michaelis M, Schubert-Zsilavecz M, Cinatl J Jr: Differential antiviral and anti-inflammatory mechanisms of the flavonoids biochanin A and baicalein in H5N1 influenza A virus-infected cells. Antiviral Res. 2013 Jan;97(1):41-8. doi: 10.1016/j.antiviral.2012.10.004. Epub 2012 Oct 23. [PubMed:23098745 ]

Showing NP-Card for Baicalein (NP0047774)

MOL for NP0047774 (Baicalein)

3D MOL for NP0047774 (Baicalein)

3D SDF for NP0047774 (Baicalein)

3D-SDF for NP0047774 (Baicalein)

PDB for NP0047774 (Baicalein)

3D PDB for NP0047774 (Baicalein)

SMILES for NP0047774 (Baicalein)

INCHI for NP0047774 (Baicalein)

Structure for NP0047774 (Baicalein)

3D Structure for NP0047774 (Baicalein)